Key West Holiday Happenings

It’s the most magical time of the year, and all of us in Key West are getting ready for your arrival with a festive list of things to do during your stay. There will be caroling, drinking, eating, shopping, lighted boat and bike parades, Santa sightings, and celebrations to ring in the New Year. There are a few naughty and nice events, pool parties, and a run with Rudolph for a good cause.  Here is the lineup of events for the 2021 Key West Holiday Season: 

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The Lighting of the Key West “Harbor Walk of Lights.”

The Holiday Season in Key West kicks off on November 24th with the Historic Seaport Lighting of the Key West “Harbor Walk of Lights.” Just steps from our resort at the Harbor Walk, Green and Elizabeth Street, the official lighting of the 2021 Key West Harbor Walk of Lights takes place. Celebrate the Maritime history of Key West with the lighting of the Fishing Buoy Christmas Tree, a Nautical Christmas Tree, and the Lobster Trap Christmas Tree.  

Stroll down the Harborwalk and enjoy the merry displays, including ship’s anchors, tropical birds, tropical fish, manatees, and animated sea turtles all lit up.

The Harborwalk of Lights is lit every evening during the holidays!

Conch Tour Train and Trolley Holiday Lights Tour
December 12-17, December 20-23, December 26, 2021.

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A must-see and fa la la la do during the holiday season – Old Town Trolley’s and Conch Tour Train Holiday Lights and Sights Tour.  A great way to get in the holiday spirit and see our island all decked out for the holidays. There will be caroling, apple cider and cookies, and complimentary magical viewing glasses. The Conch Tour Train Holiday Lights Tour is 60 minutes long and runs through December. 

Adults : $26.25
Children – 3-12 years old. $15.75

Learn more about purchasing tickets and dates for the 2021 Holiday Lights Tour.

Sugar Rum Cherry: A Burlesque Nutcracker
December 15-17, Doors open at 7 pm. The show starts at 8 pm.

Key West Holiday Happenings

Photo credit: Key West Theater

Head over to the Key West Theater on Eaton Street for a truly unique holiday burlesque version of The Nutcracker. 
Slip into your stockings and pull out your sugarplums for the outrageously cheeky production of Sugar Rum Cherry: A Burlesque Nutcracker. This naughty but nice two-act holiday reverie showcases a bevy of burlesque beauties who dance their way through the land of libations in an adult version of the holiday classic. Doors open at 7 PM, show starts at 8 PM at the Key West Theater, 512 Eaton St.  Tickets Available: $50 – $100.  Learn more

13th Annual 5k Rudolph Red Nose Run – the PJ Edition
Saturday, December 18th – 7 am – 10 am 

Run for a good cause at the 13th Annual 5k Rudolph Red Nose Run to benefit for A Positive Step of Monroe County. Put on your festive holiday jammies and join in the 13th A Positive Step 5K Rudolph Red Nose Run – the PJ Edition, taking place Saturday morning, December 18, starting and ending at the Southernmost Beach Café.  Race day check-in begins at 7:00 am with an 8:00 am start time. After the race, enjoy refreshments, prizes, and a silent auction.

Location: Southernmost Beach Cafe, 1405 Duval Street | Key West, FL 33040

Sign up, register, and run with the locals and Rudolph to benefit this good cause!  Learn more. 

Where will you be on New Year’s Eve? 

New Years Eve Around The World Party
Friday, December 31st, Noon – 9 pm | Southernmost Beach Resort

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Why wait till midnight? Head over to Southernmost Beach Resort for the New Year’s Eve Around The World Party!  There will be hourly drink specials starting at noon leading up to an early New Years’ Eve toast at 9 pm! 
Southernmost Beach Resort, 1319 Duval Street, Key West, FL 33040

Where will you be ringing in the New Year?

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Photo credit: Rob O’Neal

At midnight in Key West, you have the opportunity to watch a Conch Shell Drop at Sloppy Joe’s Bar, a New Year’s Eve Shoe Drop by Sushi at the Bourbon Street Pub/New Orleans House complex, or watch the Lowering of the Wench at Schooner Wharf Bar. So many options on one special night! Wherever you are, we wish you a safe and happy holiday season and a very Happy New Year!!

New Years Day Eve Take 2 Laser Night Pool Party
Saturday, January 1st, 6 pm – 9 pm | The Marker Key West Harbor Resort

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Happy New Year!  Let’s start the new year at our sister property,
 The Marker Key West Harbor Resort. Join us for a night of music and a fantastic laser show while you swim the night away in one of our three pools.  Papa’s Pilar will be there with drink specials and more! 

What are some of your favorite holiday events where you live? We’d love to hear about them and see some of your festive photos. Enjoy the holiday season! #somolife